Chasing a championship is every MLB team’s dream, but sometimes that all-in mentality backfires in spectacular fashion. Whether it’s trading away top prospects, handing out bloated contracts, or doubling down on a flawed roster, these win-now moves left franchises with nothing but regret.
From blockbuster deals to free-agent splurges that aged like milk, these 14 moments show how quickly an aggressive title push can go sideways. When the dust settles and the rings never come, all you’re left with is a depleted farm system, a bloated payroll, and a whole lot of “what ifs.”
14. The 2023 Padres Go All-In
The Padres built a superteam on paper, but baseball games aren’t won on spreadsheets. A star-studded lineup fell flat, and the front office was left scrambling with a huge payroll and no playoff spot to show for it.
13. Phillies Trade for Roy Oswalt in 2010
The Phillies were already loaded with talent, but they couldn’t resist adding another ace. Oswalt pitched well, but Philly came up short in October and gave up future assets for a short-lived rental.
12. Tigers Acquire David Price in 2014
Detroit tried to keep its World Series window open by adding another ace. But the team fizzled out, missed the playoffs in 2015, and began a painful rebuild soon after.
11. Mariners Trade for Erik Bedard in 2008
Seattle gave up a haul of future stars—including Adam Jones—for Bedard. Injuries and underperformance followed, and the Mariners didn’t even sniff contention.
10. Dodgers Sign Jason Schmidt in 2006
Desperate for pitching help, the Dodgers handed Schmidt a massive deal. He barely pitched due to injury, and the team got almost nothing in return.
9. Braves Trade for Mark Teixeira in 2007
Atlanta sent multiple young players to Texas—including Elvis Andrus—for a bat to push them into October. Teixeira raked, but the Braves missed the playoffs and lost him a year later.
8. Red Sox 2011 Free Agent Frenzy
Carl Crawford and Adrian Gonzalez were supposed to turn Boston into an unbeatable force. Instead, the clubhouse imploded, and the team collapsed down the stretch in spectacular fashion.
7. Mets Trade for Edwin Díaz and Robinson Canó in 2018
This was supposed to be a splashy move to kickstart contention. Instead, Canó declined quickly, Díaz initially struggled, and the Mets gave up a future star in Jarred Kelenic.
6. Angels Sign Josh Hamilton in 2012
Los Angeles gave Hamilton a monster deal, hoping to form a deadly duo with Mike Trout. Instead, injuries and personal issues derailed his stint, and the Angels never got close to contending.
5. Cubs Trade for José Quintana in 2017
The Cubs paid a steep price to land Quintana from the crosstown White Sox. Quintana was fine, but the Sox ended up with Eloy Jiménez and Dylan Cease, both of whom blossomed into stars.
4. Yankees Trade for Sonny Gray in 2017
New York believed Gray would thrive in the Bronx. He didn’t, struggling with command and never finding his footing before being dealt away for pennies on the dollar.
3. White Sox Trade for Jeff Samardzija in 2015
Chicago thought Samardzija would help launch a new contention era. He posted a mediocre season, the team underwhelmed, and they lost him in free agency after one year.
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2. Astros Trade for Carlos Gomez in 2015
Houston wanted a veteran bat to guide their young core, but Gomez never found his form. The Astros also gave up a rising star in Josh Hader, who became a dominant reliever elsewhere.
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1. Rangers Trade for Cole Hamels in 2015
Texas swung big to land Hamels, trying to catch lightning in a bottle. While Hamels pitched well, the Rangers never made a deep run—and the Phillies rebuilt around the prospects they received.
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